Macam Macam Pelarut
Macam Macam Pelarut
Macam Macam Pelarut
Abstract
Background: Lignocellulosic biomass is one of the most promising alternatives for replacing mineral resources to
overcome global warming, which has become the most important environmental issue in recent years. Furfural was
listed by the National Renewable Energy Laboratory as one of the top 30 potential chemicals arising from biomass.
However, the current production of furfural is energy intensive and uses inefficient technology. Thus, a hybrid purifica-
tion process that combines extraction and distillation to produce furfural from lignocellulosic biomass was considered
and investigated in detail to improve the process efficiency. This effective hybrid process depends on the extracting
solvent, which was selected based on a comprehensive procedure that ranged from solvent screening to complete
process design.
Results: Various solvents were first evaluated in terms of their extraction ability. Then, the most promising solvents
were selected to study the separation feasibility. Eventually, processes that used the three best solvents (toluene,
benzene, and butyl chloride) were designed and optimized in detail using Aspen Plus. Sustainability analysis was
performed to evaluate these processes in terms of their energy requirements, total annual costs (TAC), and carbon
dioxide (CO2) emissions. The results showed that butyl chloride was the most suitable solvent for the hybrid furfural
process because it could save 44.7% of the TAC while reducing the CO2 emissions by 45.5% compared to the toluene
process. In comparison with the traditional purification process using distillation, this suggested hybrid extraction/
distillation process can save up to 19.2% of the TAC and reduce 58.3% total annual CO2 emissions. Furthermore, a
sensitivity analysis of the feed composition and its effect on the performance of the proposed hybrid system was
conducted.
Conclusions: Butyl chloride was found to be the most suitable solvent for the hybrid extraction/distillation process
of furfural production. The proposed hybrid sequence was more favorable than the traditional distillation process
when the methanol fraction of the feed stream was <3% and more benefit could be obtained when that fraction
decreased.
Keywords: Biomass feedstock, Biorefinery development, Furfural, Hybrid process, Lignocellulosic biomass,
Solvent selection
*Correspondence: mynlee@yu.ac.kr
†
Le Cao Nhien and Nguyen Van Duc Long contributed
equally to this work
1
School of Chemical Engineering, Yeungnam University,
Gyeongsan 712-749, South Korea
Full list of author information is available at the end of the article
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Nhien et al. Biotechnol Biofuels (2017) 10:81 Page 2 of 12
most promising solvents are accordingly proposed. he solvents used have purities of more than 99 wt%.
potential solvents and detailed designs for producing T he solvent and feed streams are initially introduced
furfural on an industrial scale can be investigated using to an LL extractor to produce a solvent-rich stream
a framework. called the extract and an extracted-feed stream called
the rainate. The extract that contains the most furfural
Simulation in the feed is input to a distillation column to purify
Aspen Plus V9 was used to simulate the puriication pro- the furfural and recover the solvent. he following
cess for furfural production utilizing the RadFrac model sections show how diferent solvents were evaluated
for rigorous distillation and Extraction model for the LL for the hybrid extrac- tion/distillation process using the
extraction. he non-random two-liquid (NRTL) prop- systematic framework shown in Fig. 2.
erty method with binary parameters taken from the liq-
uid–liquid equilibrium (LLE) Aspen database was used to Solvent screening
calculate the liquid activity coeicients for the Extraction Because the art of solvent extraction has a long history,
model. Meanwhile, the non-random two-liquid-Hayden– and LL extraction has been practiced in a large number
O’Connell (NRTL-HOC) thermodynamic package with of industrial applications, the key principles of solvent
binary parameters taken from the vapor–liquid equilib- selection are available and well described in the literature
rium (VLE) Aspen database was used to perform a rigor- [20–22]. Moreover, several researchers investigated the
ous simulation of the distillation, in which the NRTL was extraction of furfural from an aqueous stream using the
used to calculate the liquid activity coeicients, and the acidic hydrolysis of biomass [4, 23]. On the basis of lit-
HOC equation of state was used to calculate the thermo- erature survey and heuristics, all possible solvents from a
dynamic properties of the vapor phase. he HOC equa- wide range of chemical families, including alcohols, nor-
tion reliably predicts a mixture of carboxylic acids, which mal hydrocarbons, ketones, aromatics, amines, etc., are
may occur during the solvation of polar compounds irstly generated as shown in Fig. 3. Subsequently, several
and dimerization in the vapor phase [19]. Note that the preliminary simulations are carried out in order to pre-
interaction parameters between the major components, pare a short list of candidates for detail screening step.
such as furfural–water and all solvents–water, are avail- In particular, ten potential solvents (toluene, benzene,
able in both the LLE and VLE Aspen databases. For the p-xylene, octyl acetate, decane, cyclohexane, hexene,
missing binary parameters of the remaining minor com- cyclohexene, cumene, and butyl chloride) were selected
ponents, a Universal Quasichemical Functional-Group for further consideration.
Activity Coeicients (UNIFAC) model was employed for he LL equilibrium curve plays a crucial role in design-
estimation. ing an extraction process [24]. he use of equilibrium
distribution coeicients that can screen a large number
Results and discussion of solvents is an efective and economic method for sol-
In this study, the furfural puriication process was vent screening [25]. he distribution coeicient was cal-
designed based on a production rate of 50 ktons/year. culated using the equilibrium data at a given temperature
he feed stream consisted of aqueous solutions obtained as follows [23]:
from the acidic hydrolysis reaction of the lignocellulosic
KD = [Extracted component]solvent [Extracted component]aqueous.
biomass. Table 1 lists the feed conditions, component
compositions, and product speciications [3]. All of the (1)
Table 1 Feed mixture conditions and product speciica- he distribution coeicient of the extracted compo-
tions nent (KD) is the ratio of the weight percentage (wt%) of
Component Mass fraction (wt%) the extracted component [furfural, methanol, or acetic
acid (AA)] in the solvent phase to the weight percentage
Methanol 2.0 of the extracted component in the aqueous phase. In the
Water 90.0 solvent screening step, the water–solvent equilibrium for
Acetic acid (AA) 2.0 furfural, AA, and methanol was studied, and the distri-
Furfural 6.0 bution coeicients and extraction eiciencies were com-
Furfural product purity (wt%) >99.0 pared for each solvent at 298 K. he feed low rate was
Solvent product purity (wt%) >99.0 ixed, and the solvent low rate was changed to analyze
Temperature (K) 353 the solvent eiciency. In particular, for each solvent, four
Pressure (kPa) 101 diferent cases with feed-to-solvent mass ratios of 1:0.4,
Mass flowrate (kg/h) 105,000 1:0.9, 1:1, and 1:1.1 were considered.
Nhien et al. Biotechnol Biofuels (2017) 10:81 Page 5 of 12
Fig. 3 Lists of solvents: from possible initial solvents to short list of candidates for detailed screening
Figure 4 shows the equilibrium curves of the furfural an excellent equilibrium with a very high AA concentra-
for the diferent solvents examined at 298 K. Clearly, ben- tion in the extract phase, whereas all of the remaining
zene, toluene, p-xylene, cumene, octyl acetate, and butyl solvents have unfavorable equilibrium for AA extraction.
chloride have a favorable equilibrium with high distri- In particular, with the exception of decane, the presence
bution coeicient values, whereas decane, cyclohexane, of AA in the rainate phase was always much greater
cyclohexene, and hexane show unfavorable equilibrium than that in the extract phase.
for extracting furfural. Remarkably, benzene presents Figure 6 shows the equilibrium curves of methanol for
the most favorable equilibrium with the highest distribu- the diferent solvents examined at 298 K. Although octyl
tion coeicient value for furfural extraction. Accordingly, acetate shows the most favorable result for methanol
decane, cyclohexane, hexane, and cyclohexene were extraction, the methanol concentration in the rainate
deemed unsuitable for extracting furfural from an aque- phase was much higher than that in the extract phase.
ous solution. As a result, all of the solvents tested were unsuitable for
Figure 5 presents the equilibrium curves of AA for all extracting methanol from the aqueous feed stream.
the solvents tested at 298 K. Interestingly, decane shows
valuable byproducts. Hence, a solvent’s extraction ability acetate was excluded from further consideration. Overall,
for them has less impact than for furfural. In the case of toluene, benzene, and butyl chloride were selected for the
decane, in addition to its excellent ability to extract AA, next process design step.
its performance in extracting furfural was still promising.
herefore, it was not eliminated in this step. Overall, ben- Process design
zene, toluene, p-xylene, cumene, octyl acetate, butyl chlo- In this step, the hybrid extraction/distillation processes
ride, and decane were selected for further consideration. for furfural production using the three best solvents
(toluene, benzene, and butyl chloride) selected from the
Separation feasibility previous step were designed and optimized. he aque-
If the added solvent forms azeotropes with the major ous feed stream, which was cooled down to 313 K, and
extracted components, the design of the solvent regen- the solvent were irst input to an extractor to produce an
eration part will become much more complex, lead- extract composed of a large portion of furfural in the feed
ing to economic infeasibility. herefore, in this step, the and a rainate. he extract was then introduced to a dis-
seven solvents selected in the solvent screening step were tillation column to separate the furfural and solvent. Note
investigated to determine whether they formed azeo- that in this hybrid process, the rainate from the extrac-
tropes with the feed components to examine the ease of tor consists of water loaded with AA and methanol which
separation. Originally, furfural and water form a binary are delivered into a wastewater treatment plant. In par-
heterogeneous azeotrope (35.5 wt% furfural) at 371 K ticular, AA is not collected in both hybrid and traditional
and 101 kPa. Table 3 lists all of the azeotropes formed distillation processes while methanol is a by-product in
between the added solvents and feed components, the distillation process. Comparison of both processes
which were investigated based on the Aspen database will be discussed further in sustainability analysis section.
at a pressure of 101 kPa. Because the major task of the For design speciications, all of the design variables such
hybrid extraction/distillation process is the separation as a total number of trays, feed location, and feed-to-sol-
of the furfural and solvent mixture, forming an azeo- vent ratio were manipulated through sensitivity analyses
trope between the furfural and solvent will lead to either to improve the process eiciency while maintaining the
infeasible separation or economic infeasibility. herefore, product purities and recoveries. To make a fair com-
the p-xylene, decane, and cumene solvents were elimi- parison, the furfural recovery was 99.9 wt% through the
nated because they formed homogeneous azeotropes extractor and 99.0 wt% through the distillation column,
with furfural. Note that in all cases except octyl acetate, resulting in the same furfural production rate in all cases.
the extracts contained a very small amount of water (less
than 100 kg/h). hus, the efect of the heterogeneous aze- Toluene solvent process
otropes formed between the water and solvents was neg- he feed stream obtained from the biomass hydroly-
ligible. However, the extract of the octyl acetate process sis process was irst cooled down to 313 K before being
contained quite a large amount of water (600 kg/h when introduced to the extractor (E1). Herein, the LL extrac-
the feed/solvent mass ratio was 1:1). he fact that water tion process produced a rainate at the bottom and an
not only forms a heterogeneous azeotrope with furfural extract containing furfural at the top. he extract was
but also with octyl acetate will make the following distil- then inputted to a distillation column (D1) to deliver a
lation process more complex and costly. herefore, octyl top stream of toluene and a bottom stream of the desired
furfural. Figure 8 shows the key design and process Butyl chloride solvent process
parameters of the optimized hybrid extraction/distil- Similar to the toluene process, the cooled feed stream and
lation process using the toluene solvent. Because of the butyl chloride solvent in the butyl chloride process were
high furfural extraction ability, only 44,000 kg/h of tolu- input to an extractor to generate a solvent-rich phase and
ene corresponding to a feed-to-solvent ratio of 1:0.4 was rainate phase. he butyl chloride-rich stream was then
suicient to extract 99.9 wt% of the furfural in the feed. introduced to a distillation column (D2) to isolate the
T he simulation results showed that D1 required furfural at the desired purity of 99 wt% and recover butyl
medium- pressure steam for its reboiler and had an chloride. Figure 9 presents the key design and process
energy con- sumption of 11,354 kW. parameters of the optimized hybrid extraction/distillation
T = 368K
P = 101 kPa
Q = 11,508 kW
43,760 kg/h
50,030 kg/h 1 1 wt% water
Q = 4645 kW 87 wt% toluene Toluene 99 wt% toluene
105,000 kg/h 353K 313K 1 13 wt% furfural 22
2 wt% methanol Rich solvent
90 wt% water Feed D1
2 wt% AA
6 wt% furfural
Toluene E1 Aqueous
26 6270 kg/h
5 98,970 kg/h
44,000 kg/h 1 wt% toluene
T = 433K Furfural 99 wt% furfural
P = 101 kPa
P = 122 kPa
Q = 11,354 kW
Fig. 8 Schematic diagram of hybrid extraction/distillation process using toluene solvent
T = 322K
101 kPa
7802 kW
61,502 kg/h
67,773 kg/h 1
99 wt% butyl chloride
Q = 4645 kW 90 wt% butyl chloride Butyl
105,000 kg/h 353K 9 wt% furfural chloride
313K 1 8
2 wt% methanol
90 wt% water Feed Rich solvent
2 wt% AA D2
6 wt% furfural
Butyl chloride E2 Aqueous
11
62,000 kg/h 6 99,228 kg/h 6270 kg/h
Furfural 99 wt% furfural
P = 101 kPa T = 433K
P = 111 kPa
Q = 8326 kW
Fig. 9 Schematic diagram of hybrid extraction/distillation process using butyl chloride solvent
Nhien et al. Biotechnol Biofuels (2017) 10:81 Page 9 of 12
T = 341K
P = 101 kPa
Q = 5576 kW
Benzene E3 Aqueous
9
4 6270 kg/h
42,000 kg/h 99,061 kg/h
T = 433K Furfural 99 wt% furfural
P = 101 kPa 1 wt% benzene
P = 111 kPa
Q = 6476 kW
Fig. 10 Schematic diagram of hybrid extraction/distillation process using benzene solvent
Nhien et al. Biotechnol Biofuels (2017) 10:81 Page 10 of 12
where Qproc is the heat duty requirement of the system, and TCE, respectively, compared to the toluene process.
and λproc (kJ/kg) and hproc (kJ/kg) are the latent heat and Toxicity and eco-toxicity are main undesirable features of
enthalpy of the steam, respectively. he lame, stack, and butyl chloride as a solvent. But if we look at its potential
ambient temperatures were TFTB (2073 K), Tstack (433 K), contribution to a global warming aspect, its signiicant
and T0 (298 K), respectively. CO2 emission reduction efect would give butyl chloride
Table 4 lists the key results for the carbon footprint and most attractive and advantageous feature as a solvent. As
economic performance, including TAC, TIC, and TOC. shown in the present study, the hybrid extraction and dis-
Remarkably, the benzene process showed the best perfor- tillation process using butyl chloride solvent can reduce
mance, achieving savings of 24.1, 60.7, and 57.1% in terms CO2 emission up to 58.3% equivalently compared to the
of TIC, TOC, and TAC, respectively, as well as a reduction traditional distillation process. Its outstanding perfor-
of 43.0% in the carbon footprint compared to the toluene mances on CO2 reduction due to enhanced energy ei-
process. However, because benzene is a human carcino- ciency with the high recovery of 99.71 wt% can be a worth
gen, its use as a solvent in the industry needs to be care- consideration as a possible option of industrial furfural
fully controlled. In recent years, it has been supplanted separation technology. Of course, to take into account its
by other safer solvents. herefore, we here propose butyl potential problem associated with the toxicity, it should
chloride solvent as a good choice for the hybrid purii- be assumed that the process must be designed and oper-
cation process of furfural because its process can save ated to satisfy more strict safety and sealing regulation
17.1, 26.8, 25.9, and 26.7% in terms of TIC, TOC, TAC, like as other processes handling harmful species.
Table 5 Comparison of key results between the hybrid and traditional distillation processes and their improved pro-
cesses
Process TCE TIC TOC TAC Methanol Solvent TAC*
(ton/year) (k$/year) (k$/year) (k$/year) proit (k$/year) cost (k$/year) (k$/year)
butyl chloride taken from global world market data were signiicant efect on the hybrid design. In contrast to the
$0.276/kg [29] and $1.1/kg, respectively [30]. Meanwhile, hybrid process, as the methanol fraction increased, the
the proit from selling methanol was assumed to be 50% TAC* of distillation decreased signiicantly. his means
of the total sales value. that the additional investment and operating costs for
he results showed that the hybrid extraction/distilla- the methanol separation column due to an increase in
tion process using the butyl chloride solvent can produce the methanol lowrate are much lower than the proit
TAC savings of up to 19.2% compared to the traditional from selling methanol. Figure 11 illustrates the beneit of
distillation process. Remarkably, the hybrid process was the hybrid process compared to the distillation process
also more eco-friendly, accounting for a 58.3% reduction with diferent scenarios for the byproduct composition.
in the carbon footprint, which is closely linked to energy Remarkably, the hybrid process is more favorable than the
requirements, compared to the distillation process. distillation process when the methanol fraction of the feed
Furthermore, the results shown in Table 5 also indi- stream decreases and does not produce any beneit. How-
cated that the improved hybrid process, which utilizes ever, the distillation process is a better choice when the
the heat of the distillation bottom stream to preheat its methanol fraction is larger than 3 wt%. It is worth noting
feed, can save up to 9.6% of the TAC as compared to the that the present study used the UNIFAC model to estimate
improved distillation process using integrated and inten- the missing binary parameters of several minor compo-
siied techniques, which was studied by Nhien et al. [4]. nents. he experimental validation is essential to be con-
sidered as a next step for conirming process performance,
Sensitivity analysis leading to more reliable results for real implementation.
In a lignocellulose-based process, breaking down the
complex cellulose–hemicellulose–lignin structure of the Conclusions
lignocellulosic biomass could lead to an inherent uncer- A hybrid extraction/distillation process was proposed to
tainty in the stream composition, which could have a successfully improve the traditional process of furfural
major efect on the suggested design. herefore, a sensi- production, which is energy intensive. Promising solvents
tivity analysis was performed to improve the robustness were suggested through a comprehensive procedure for
of the proposed results. he aqueous feed of the present solvent selection that ranged from solvent screening to
puriication process produced from furfural reactors complete process design. he economic and environmen-
comprises about 6 wt% furfural, 90 wt% water, and 4 wt% tal performances of three processes using the most prom-
byproducts (methanol and AA). In this analysis, the fur- ising solvents (toluene, benzene, and butyl chloride) were
fural and water fractions were ixed, and ive scenarios evaluated for a fair comparison. Overall, benzene and
for the methanol and AA composition of the feed were butyl chloride were found to be the most suitable solvents
explored to determine how the byproduct composition for furfural production because their processes could
afects the proposed design for the furfural puriication achieve TAC savings of 71.3 and 44.7%, respectively, com-
process. Table 6 lists the key results of the sensitivity pared to the toluene process. However, because of ben-
analysis of the hybrid and distillation processes. zene’s obvious toxicity, butyl chloride was proposed as a
In the hybrid process, as the methanol fraction is
increased, the rate of solvent makeup and methanol loss
also increase. As a result, the TAC* gradually increases
from $5.4 million up to $6.2 million with respect to a
methanol fraction increase from 0 to 4 wt%. Note that
changes in the byproduct composition did not have a
Hybrid process
Solvent makeup (ton/year) 1240 1320 1416 1568 1880
TAC* (k$/year) 5487 5575 5680 5848 6191
Distillation process
Methanol product rate 0 8356 16,712 25,068 33,424
(ton/year) Fig. 11 Effect of methanol–acetic acid composition on TAC savings
TAC* (k$/year) 8778 7913 7031 6150 5267 of hybrid process
Nhien et al. Biotechnol Biofuels (2017) 10:81 Page 12 of 12
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School of Chemical Engineering, Yeungnam University, Gyeongsan 712-749,
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